Natural Product (NP) Details

General Information of the NP (ID: NP3555)
Name
Evodiamine
Synonyms
Evodiamine; 518-17-2; d-Evodiamine; (+)-Evodiamine; UNII-C01825BVNL; C01825BVNL; CHEBI:4948; Evodiamine, 98%; (S)-14-methyl-8,13,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one; Evodiamine, Evodia rutaecarpa; PubChem18244; Evodiamine, (+)-; Evodiamine,(S); (13bS)-14-methyl-8,13,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one; Evodiamine(Isoevodiamine)/; MLS006011787; SCHEMBL682158; CHEMBL463165; DTXSID10966123; ZINC898159; BCP02282; HY-N0114; ABP000693; BBL033833; STK801981; AKOS005622478; CS-6161; MCULE-2788564607; (S)-14-methyl-7,8,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(13H)-one; SMR001934404; VS-12304; N1600; C09187; 518E172; Q-100579; Q27894193; Evodiamine, European Pharmacopoeia (EP) Reference Standard; 14-Methyl-8,13,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one; (1S)-21-METHYL-3,13,21-TRIAZAPENTACYCLO[11.8.0.0(2),(1)?.0?,?.0(1)?,(2)?]HENICOSA-2(10),4,6,8,15,17,19-HEPTAEN-14-ONE; (1S)-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one; Indol(2',3':3,4)pyrido(2,1-b)quinazolin-5(7H)-one, 8,13,13b,14-tetrahydro-14-methyl-, (13bS)-; Indol(2',3':3,4)pyrido(2,1-b)quinazolin-5(7H)-one, 8,13,13b,14-tetrahydro-14-methyl-, (S)-
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Species Origin Evodia rutaecarpa Bentham ...     Click to Show/Hide
Evodia rutaecarpa Bentham
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Sapindales
Family: Rutaceae
Genus: Tetradium
Species: Evodia rutaecarpa Bentham
Disease Lung cancer [ICD-11: 2C25] Investigative [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.635
 
MDCK Permeability
 -4.598
 
PAMPA
 - -
 
HIA
 - - -
 
Distribution
VDss
 0.061
 
PPB
 96.1%
 
BBB
 ++
 
Metabolism
CYP1A2 inhibitor
 - -
CYP1A2 substrate
 +++
CYP2C19 inhibitor
 +++
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 +++
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 +++
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - -
HLM Stability
 +++
 
Excretion
CLplasma
 7.39
 
T1/2
 0.99
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 ++
 
FDAMDD
 +
 
Respiratory
 +++
 
Human Hepatotoxicity
 +++
 
Ototoxicity
 +++
 
Drug-induced Nephrotoxicity
 +++
 
Drug-induced Neurotoxicity
 ++
 
Hematotoxicity
 +
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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Formula
C19H17N3O
PubChem CID
442088
Canonical SMILES
CN1C2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3
InChI
1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3/t18-/m0/s1
InChIKey
TXDUTHBFYKGSAH-SFHVURJKSA-N
CAS Number
CAS 518-17-2
ChEBI ID
CHEBI:4948
Herb ID
HBIN026264
SymMap ID
SMIT01413
TCMSP ID
MOL003958
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          TNF-related apoptosis inducing ligand      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression CTNNB1  Molecule Info 
Pathway MAP
                    In-vitro Model U-87MG ATCC CVCL_0022 Glioblastoma Homo sapiens
                    Experimental
                    Result(s)		 Evodiamine sensitizes U87 glioblastoma cells to TRAIL via the death receptor pathway.
Target and Pathway
Target(s) Transient receptor cation channel V1 (TRPV1)  Molecule Info  [3]
KEGG Pathway Neuroactive ligand-receptor interaction Click to Show/Hide
2 Inflammatory mediator regulation of TRP channels
NetPath Pathway IL2 Signaling Pathway Click to Show/Hide
Pathway Interaction Database Trk receptor signaling mediated by the MAPK pathway Click to Show/Hide
2 Trk receptor signaling mediated by PI3K and PLC-gamma
Reactome TRP channels Click to Show/Hide
References
Reference 1 Evodiamine suppresses non-small cell lung cancer by elevating CD8 + T cells and downregulating the MUC1-C/PD-L1 axis. J Exp Clin Cancer Res. 2020 Nov 19;39(1):249.
Reference 2 Evodiamine sensitizes U87 glioblastoma cells to TRAIL via the death receptor pathway. Mol Med Rep. 2015 Jan;11(1):257-62.
Reference 3 Essential role of transient receptor potential vanilloid type 1 in evodiamine-mediated protection against atherosclerosis. Acta Physiol (Oxf). 2013 Feb;207(2):299-307.
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